Conceptual parallels and structural similarities between Pauline Christianity and Greco-Roman philosophical schools often produce fruitful comparison. Paul’s understanding of moral progress (p????p?) compared with moral philosophers is a particularly interesting conceptual parallel, shedding light on his view of moral development. However, it is the contention of this essay that p????p? merits consideration not just as a conceptual parallel, as others have already shown, but as a mark of structural similarity between the Pauline tradition of the Pastoral Epistles and competing philosophical schools. Comparing and contrasting p????p? in 1–2 Timothy, Philo, Plutarch, and Epictetus, this essay clarifies the debate among competing philosophical schools concerning: whether or not p????p? could be measured, how p????p? was measured and the educational requirements that made p????p? possible. This investigation suggests that 1–2 Timothy represent a particularly scholastic strand of the Pauline legacy that purported scribal literacy among its leaders.